Beach and Cottage Hill

The Beach and Cottage hill section of town was originally part of the Winthrop Farm, which remained in the Winthrop Family until the 1750’s. While 4 houses were built on Shirley Street in the late 1840’s and early 50’s, this area did not begin to be developed until the 1870’s. John Tewksbury built one of these houses in about 1846 at the northern base of Cottage Hill and today it is the rear portion of the Inn at Crystal Cove.

At first, a couple of summer tent encampments were set up near the beach where a few families from inland could enjoy the ocean breezes. Then in 1875, Dr. Sam Ingalls purchased 43 acres along the beach and laid out a summer colony of seaside cottages which he called Ocean Spray. All the streets were identified with nautical names that are still with us, Neptune, Mermaid, Coral, Trident, Sea Foam, Wave Way, Pearl and Dolphin. Many of the original cottages at Ocean Spray were of the same general design and, although somewhat modified, can be seen today. All deeds for the lots contained a prohibition clause, which is no longer enforceable, to prevent drinking in the colony.


Shortly thereafter, the section of the beach from Ocean Spray to Cottage Hill was purchased and named Atlantic Wave. In this area, the Tewksbury Memorial Pavilion was erected on Tewksbury Street in 1887 for summer services.

In 1878, Cottage Hill was purchased and then in 1882 surveyed for house lots. In 1883, William Rice purchased Cottage Hill and had Whitman & Howard lay out the Streets, as we know them to day. Also, in 1883/4, access to the area was improved by the construction of a bridge from Washington Avenue to connect with Shirley Street at Delby’s corner.

In 1886, the clubhouse for the newly formed Great Head Yacht Club (1884) was built behind a pier at the end of Tewksbury Street. It was subsequently moved in 1890 to the current location and renamed in 1891 as The Winthrop Yacht Club. The present clubhouse was built in 1904 after a fire destroyed the earlier building.


A picture of the Winthrop Shore Drive beach area as it appeared in the early part of the 1900’s is shown below.